50 Greatest Comedies of the 21st Century

From rom-coms to raunch-coms, 'Anchorman' to 'Wet Hot American Summer' – the funniest movies of the new millennium so far

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'Sideways' (2004)
Fox Searchlight Pictures/Kobal/REX/Shutterstock39/50

39. 'Sideways' (2004)

Alexander Payne's oenophilic comedy has likely put a dent in merlot sales forever, but it's aged into a quaffable vintage, courtesy of Paul Giamatti's performance as a self-loathing wine connoisseur. As he and his soon-to-be-married friend (Thomas Haden Church) venture to California wine country for a bachelor weekend, Sideways develops a sharp buddy-movie dynamic between a pungent misanthrope and a pleasure-seeking horndog. There's sweetness at the film’s core, drawn out in his boozy courtship of a fellow enthusiast (Virginia Madsen), but Payne gets a buzz off Giamatti's ornery belligerence, which at one point has him lunging for the wine-tasting spittoon. ST

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